Vacation rentals in Chicago

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Chicago vacation rentals
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Best Vacation rentals and Airbnb offers in Chicago

Top-Rated Vacation Rentals near the City Center in Chicago

From vibrant downtown areas to historic streets, these Chicago vacation rentals put you close to everything worth seeing.

South Loop 2br Getaway With Smart Tvs & Optional Parking Near Mccormick Place, Museum Campus & Downtown - Chicago
9.6 104 reviews

South Loop 2br Getaway With Smart Tvs & Optional Parking Near Mccormick Place, Museum Campus & Downtown

apartment, Chicago
This Chicago apartment is conveniently located near McCormick Place, just a short distance from the Field Museum and the Art Institute. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom apartment comfortably accommodates six guests with its 850 square feet of space. Enjoy features like a fitness center, free Wi-Fi, a fully equipped kitchen, and optional parking for your convenience.
Old Town Studio With High End Amenities - Chicago
10 2 reviews

Old Town Studio With High End Amenities

apartment, Chicago
This modern studio suite is located in a prime Chicago district, offering convenient access to major landmarks and attractions within this bustling city. This pet-friendly apartment features a fully-equipped kitchen, spa-inspired bathroom, in-suite laundry, complimentary WiFi, and access to a fitness center, seasonal outdoor heated pool, hot tub, and on-site entertainment including shuffleboard, ping pong, and arcade games, with 24/7 concierge service available for up to 3 guests.
Livn Millennium Park Downtown Chicago Studio - Chicago
8.5 35 reviews

Livn Millennium Park Downtown Chicago Studio

studio, Chicago
This downtown Chicago studio apartment is located a 6-minute walk from Millennium Station and within half a mile of the city center.
This 300-square-foot studio offers air conditioning, complimentary WiFi, a full kitchen with a dishwasher and microwave, and accommodates up to 3 guests.
Spacious Studio In Little Italy, Near West Loop - Chicago
10 80 reviews

Spacious Studio In Little Italy, Near West Loop

apartment, Chicago
This studio apartment is located in Chicago, just a short walk from the Magnificent Mile and Millennium Park, offering easy access to the city's best shopping, dining, and attractions. Guests consistently rate this studio as excellent for its cleanliness, location, and overall experience.
The apartment features a king-sized bed and can comfortably accommodate two guests. It comes equipped with a kitchenette featuring a dishwasher, a modern bathroom with a washer/dryer, and a comfortable living space with a smart TV and reliable Wi-Fi, perfect for both relaxation and work.

Where to stay in Chicago?

The Loop

The Loop is Chicago's central business district, famous for its architecture and iconic skyscrapers, such as the Willis Tower. Just a short walk from the Loop, you can visit Millennium Park, an urban park featuring the famous sculpture "The Bean". In addition, the area is well connected by public transport, providing easy access to other Chicago attractions.

Gold Coast

Gold Coast is a historic district with beautiful mansions and buildings of neo-gothic and art deco architectural style. Tourists can stroll along the shopping avenue Oak Street, where renowned designer boutiques and luxury jewelry stores are located. Lincoln Park and the famous Lincoln Park Zoo are just a few minutes' walk away. Gold Coast is also known for its proximity to the beaches of Lake Michigan.

Wicker Park

Wicker Park is a neighborhood famous for its hipster vibe. It is full of art galleries, vintage venues and independent coffee shops. In addition, the location is notable for Wicker Park, a stunning green space that offers enriching outdoor recreational opportunities, such as a skating rink, playground and more.

Lakeview

Lakeview is a Lake Michigan neighborhood known for its lively nightlife, with an abundance of bars, clubs and restaurants to suit all tastes. You can also enjoy Lake Michigan, stroll down Broadway Avenue, where there are theaters and thrift stores, and visit Wrigley Field, the flagship stadium of the Chicago Cubs.

Lincoln Park

Lincoln Park is a neighborhood located north of downtown Chicago. It is known for having classic and refined style houses and apartments, with brick and stone facades. It is an ideal place for those seeking elegance and nature, with a variety of parks, gardens and ponds. It also has several places of interest, such as the Lincoln Park Zoo, the Lincoln Park Conservatory and the Chicago History Museum.

West Loop

The West Loop, once an industrial hub, has transformed into the culinary capital of Chicago, featuring a wide range of top-rated restaurants and chic bars. Additionally, the Fulton Market District is located in the neighborhood. Apart from its stylish ambience, the West Loop is recognized for its reinvigorated industrial architecture.

Logan Square

Logan Square is a diverse neighborhood in Chicago. This neighborhood is noted for its arts scene and its wide variety of ethnic restaurants, bars and cafes. It has several points of interest, such as the Logan Square Farmers Market, a market that offers local and organic produce every Sunday; the Logan Theatre and the Comfort Station, a former trolley station converted into a cultural space.

Hyde Park

Hyde Park, positioned in the south of Chicago downtown, houses the University of Chicago and the notable Rockefeller Memorial Chapel. Additionally, the neighborhood is also home to the Oriental Museum and the Museum of Science and Industry at the university. Besides, Hyde Park is renowned for its captivating Jackson Park and the Palace of Fountains.

Pilsen

Pilsen is a neighborhood famous for its large Mexican population. The city is historically decorated with many murals created by local artists that adorn its streets contributing to its distinctive and artistic atmosphere. In addition, Pilsen boasts the National Museum of Mexican Art, which exhibits numerous works of art created by artists of Mexican and Latin American descent.

Best Chicago vacation rentals with air conditioning

Fulbrix Bright Designer Apartments With West Loop Views - Chicago
9.3 53 reviews

Fulbrix Bright Designer Apartments With West Loop Views

apartment, Chicago
This apartment is located in the West Loop neighborhood of Chicago, a 17-minute walk from the United Center and within 2 miles of both Union Station and Millennium Station, making it easy to explore the city. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment offers 2 bedrooms, 2 bathrooms, and a spacious 1350 square feet of living space. Guests can enjoy amenities like a swimming pool, garden, terrace, parking, and a fully equipped kitchen with a dishwasher, perfect for relaxing and enjoying your stay.
Lovely 4-bedroom Apartment! 15 Mins From Downtown - Chicago
8.9 74 reviews

Lovely 4-bedroom Apartment! 15 Mins From Downtown

apartment, Chicago
This 4-bedroom apartment is located in a multicultural neighborhood in Chicago, just minutes from the expressway and a short drive from Lake Shore Drive, offering easy access to downtown and scenic views of the city skyline. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This comfortable home features 3 queen beds and 1 full bed, accommodating up to 8 guests. The apartment comes fully equipped with a kitchen, air conditioning, parking, and free Wi-Fi, ensuring a pleasant and convenient stay.
Cozy Charming Art   Food Close To Train   Parking! - Chicago
9.8 108 reviews

Cozy Charming Art Food Close To Train Parking!

apartment, Chicago
This apartment is located in Chicago's Pilsen neighborhood, a lively area known for its Mexican culture and art scene, just 3.2 miles from downtown. Guests have consistently rated this rental as excellent.
This 2-bedroom, 1-bathroom apartment offers 700 square feet of space and comfortably accommodates up to four guests. The apartment features modern amenities, including a full kitchen, washer and dryer, a private entrance, a shared patio, and free parking.
Urban Oasis In Vibrant Gold Coast - Chicago
9.9 149 reviews

Urban Oasis In Vibrant Gold Coast

apartment, Chicago
The Walton Residence is a charming apartment located in Chicago's Gold Coast neighborhood, just steps from the Magnificent Mile and the upscale boutiques of Oak and Rush Street. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
This one-bedroom apartment comfortably accommodates two guests and features a fully equipped kitchen with a refrigerator, microwave, and dishwasher. Enjoy amenities like air conditioning, internet access, and a pet-friendly environment, making your stay in Chicago comfortable and convenient.

Frequently Asked Questions about vacation rentals in Chicago

  • What should a first-time visitor not miss in Chicago, IL?

    You definitely can't miss a visit to Millennium Park and seeing Cloud Gate, also known as "The Bean." The Art Institute of Chicago is another must-see for any art lover. And of course, no trip to Chicago is complete without a deep-dish pizza, so be sure to try one at Lou Malnati's or Pizzeria Bebu.
  • What are the best Airbnb and vacation rentals in Chicago?

  • What's the best district to book a vacation rental in Chicago?

    The best district to book a vacation rental in Chicago is the Magnificent Mile. It offers a central location with easy access to popular attractions, shopping, and dining options.
  • Which neighborhood in Chicago, IL should you consider for a vacation rental?

    For a vibrant and walkable neighborhood with tons of restaurants and shops, check out Wicker Park or Bucktown. If you want to be close to the lakefront and beaches, consider Lincoln Park or Lakeview. For a more historic feel, try the Gold Coast or River North.
  • What are the most popular Airbnbs in Chicago?

  • Where can families find local cuisine in Chicago?

    Chinatown and Pilsen are great neighborhoods for trying local cuisine.
  • What are the top family-friendly attractions in Chicago, IL?

    The Lincoln Park Zoo is a great free option with plenty of animals for kids to see. The Shedd Aquarium is a bit more expensive, but it's a fantastic experience with a wide variety of marine life. And the Field Museum is always a hit with dinosaur exhibits and other fascinating displays.
  • What are the best vacation rentals with a pool in Chicago?

  • Are there any playgrounds or parks in Chicago suitable for families?

    Grant Park and Millennium Park have playgrounds and parks suitable for families.
  • When is the best time to book a vacation rental in Chicago, IL?

    The best time to book a vacation rental in Chicago is usually in the shoulder seasons, like spring or fall. You'll get better deals and avoid the crowds of summer. If you're looking for the best weather, June to August is the warmest, but expect higher prices and more tourists.
  • What are the best rentals for families and kids in Chicago?

  • Which restaurants in Chicago offer the best traditional local cuisine?

    The best restaurants in Chicago for traditional local cuisine include Lou Malnati's for deep-dish pizza, Portillo's for Chicago-style hot dogs, and The Publican for delicious pork dishes.
  • What events or festivals should visitors check out in and around Chicago, IL?

    Chicago has events all year round. In the summer, you can catch the Chicago Blues Festival or the Taste of Chicago. In the fall, there's the Chicago Marathon and the Magnificent Mile Lights Festival. And in the winter, the Christkindlmarket is a fun holiday tradition.
  • What are the best rentals or Airbnbs with a jacuzzi in Chicago?

  • What are the must-try local dishes in Chicago?

    Must-try local dishes in Chicago include the iconic Chicago-style deep-dish pizza, Italian beef sandwiches, and Garrett Popcorn's famous Chicago Mix.
  • What are the best budget-friendly activities in Chicago, IL?

    Take a walk or bike ride along the Lakefront Trail, which stretches for miles along Lake Michigan. Visit the free museums, like the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry. And enjoy a picnic in Millennium Park, where you can also see Cloud Gate and Crown Fountain.
  • What are the local expectations around tipping at restaurants and food stalls in Chicago?

    In Chicago, it's customary to tip around 15-20% at restaurants and food stalls. However, always check the bill for any included gratuity, especially for larger groups.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a popular choice for walking and biking, offering stunning views of Lake Michigan. For a more urban experience, try the 606, a former railway line transformed into a scenic park. And for a historical journey, walk the Chicago Riverwalk, which offers views of the city's iconic architecture.
  • Yes, famous stadiums like Wrigley Field and Soldier Field offer tours and behind-the-scenes experiences.

    Are there any famous stadiums or sports arenas that offer tours or behind-the-scenes experiences in Chicago?
  • Are there pet-friendly attractions in Chicago, IL?

    Yes, there are many pet-friendly attractions in Chicago. The Lincoln Park Zoo is dog-friendly, and many restaurants and cafes have outdoor patios where you can bring your furry friend. You can also find dog parks throughout the city.
  • Are there museums or landmarks related to famous athletes or sporting moments in Chicago?

    Chicago has the Chicago Sports Museum and the Michael Jordan statue outside the United Center.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy than a hotel room. You can also save money by cooking your own meals. And you can often find rentals in convenient locations, close to attractions and public transportation.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a great city for sports fans. You can catch a Cubs game at Wrigley Field, a White Sox game at Guaranteed Rate Field, or a Bulls game at the United Center. The city is also home to the Blackhawks (hockey), the Bears (football), and the Fire (soccer).

Popular destinations

Guest-Favorite Vacation Rentals with a Terrace in Chicago

Take in sweeping views of the Chicago River or the iconic skyline from your private balcony. These vacation rentals offer the perfect outdoor space to enjoy a morning coffee or an evening drink above the vibrant city streets.

Gothic-meets-mid-century 2br In Lakeview | Statment Kitchen + Dining For 4 - Chicago
No reviews

Gothic-meets-mid-century 2br In Lakeview | Statment Kitchen + Dining For 4

apartment, Chicago
This 2-bedroom coach house is located in Chicago's Lakeview district, 0.5 miles from the brown line 'L' train and a 7-minute drive to Wrigley Field.
This 750-square-foot apartment accommodates up to 4 guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace, and parking.
Cozy 2-bedroom Apartment In Pilsen Chicago - Chicago
10 4 reviews

Cozy 2-bedroom Apartment In Pilsen Chicago

apartment, Chicago
This 2-bedroom, 1-bathroom apartment in Chicago's Lower West Side offers excellent walkability to the Pink Line train and bus stops, with downtown Chicago just a 15-minute drive away, providing convenient access to attractions like Michigan Avenue, Navy Pier, the Field Museum of Natural History, and the Museum of Science and Industry, as well as event venues such as the United Center and McCormick Place. Guests will enjoy private full apartment access with a keypad entry, a full kitchen, living room, and complimentary Wi-Fi, with numerous dining options available in the neighborhood and a guest capacity of six.
Spacious Modern 3br  Topfloor + Parking - Chicago
10 8 reviews

Spacious Modern 3br Topfloor + Parking

apartment, Chicago
This 3-bedroom apartment in Chicago's Edgewater district is a 15-minute walk to Lake Michigan and a 4-minute drive to the Aragon Ballroom, with Granville Station and Loyola Station both within a 15-minute walk.
This Edgewater rental accommodates up to 5 guests and features a private garden, terrace, free Wi-Fi, a full kitchen with a dishwasher, and in-unit laundry.
Modern 2br Oak Lawn Home - Easy Commute To Chicago, Perfect For Longer Stays - Chicago
10 1 review

Modern 2br Oak Lawn Home - Easy Commute To Chicago, Perfect For Longer Stays

apartment, Oak Lawn
This Oak Lawn vacation home is conveniently located near the Chicago Ridge Mall (0.8 miles), Advocate Christ Medical Center (under 6 miles), and SeatGeek Stadium (under 6 miles), offering easy access to shopping, healthcare, and entertainment.
This 1,120-square-foot house features two bedrooms, one bathroom, and can comfortably accommodate four guests, boasting a swimming pool, spa, and fully equipped kitchen including a dishwasher, plus free Wi-Fi and a Smart TV.

Neighborhoods and points of interest in Chicago

Choose the Right Family-Friendly Vacation Rentals in Chicago

Find a spacious home base near Millennium Park or the Shedd Aquarium. These rentals offer plenty of room for the kids and easy access to the Lakefront Trail, ensuring a smooth and entertaining stay for all ages.

Light-filled Duplex On North Side - Free Parking - Chicago
9.9 78 reviews

Light-filled Duplex On North Side - Free Parking

apartment, Chicago
This three-bedroom, two-bathroom duplex apartment is located in Lincoln Square, a neighborhood in Chicago, just one block from Giddings Plaza and a five-minute walk from the Western Brown Line "L" stop. This family-friendly apartment offers a fully equipped kitchen, a separate living area, a private patio, and a game room with pinball machines, a foosball table, and a Nintendo 64.
4br Luxury Modern Apartments - Envitae Hotel - Chicago
9.9 28 reviews

4br Luxury Modern Apartments - Envitae Hotel

apartment, Chicago
This new luxury condo in downtown Chicago offers proximity to dining, shopping, and attractions, with easy access to public transport.
This spacious 4-bedroom, 3-bathroom residence sleeps 10 guests and features spectacular city views, a fully equipped kitchen with stainless steel appliances, in-unit laundry, and complimentary starter toiletries and kitchen supplies.
In The Heart Of Andersonville-steps From Clark St. - Chicago
10 129 reviews

In The Heart Of Andersonville-steps From Clark St.

apartment, Chicago
This three-bedroom Chicago apartment rental in Andersonville is steps from Clark Street's shops and restaurants.
The first-floor unit sleeps six, features a well-equipped kitchen with granite countertops and a chef's stove, a private backyard with grill, and a workspace with an iMac and 4k monitor; guests can enjoy fast Wi-Fi, streaming services, and convenient access to public transportation.
Medical District 2br With Jacuzzi & Parking - Chicago
9.8 18 reviews

Medical District 2br With Jacuzzi & Parking

apartment, Chicago
This Chicago apartment rental is ideally situated near the city's downtown area and Medical District, within easy reach of the United Center (1.1 miles), Union Station (2.6 miles), and Willis Tower.
The 1190-square-foot, two-bedroom, two-bathroom unit comfortably sleeps seven guests and features a fully equipped kitchen, free Wi-Fi, on-site parking, and air conditioning.

Best Chicago vacation rentals with parking

Space&style New Rehab, First Flr + Bsmt Of Duplex, Driveway Prkng, Walk To Train - Chicago
10 15 reviews

Space&style New Rehab, First Flr + Bsmt Of Duplex, Driveway Prkng, Walk To Train

apartment, Oak Park
Disco Cowboy 6br | Wrigley | Sleeps 16 | Game Room - Chicago
9.9 38 reviews

Disco Cowboy 6br | Wrigley | Sleeps 16 | Game Room

apartment, Chicago
Belmont House, Classy & Chic/walk To Wrigley Fld - Chicago
9.6 303 reviews

Belmont House, Classy & Chic/walk To Wrigley Fld

apartment, Chicago
2 Bedroom Apartment In Pilsen - Chicago
9.4 222 reviews

2 Bedroom Apartment In Pilsen

apartment, Chicago

Our Favorite 5-Star Vacation Rentals in Chicago

Experience the Gold Coast lifestyle in these premier rentals featuring designer finishes and high-end amenities. These upscale homes place you moments from the Magnificent Mile and the city’s finest Michelin-starred dining.

Classic Posh Home Chicago Roscoe Village+ Wrigley - Chicago
9.9 106 reviews

Classic Posh Home Chicago Roscoe Village+ Wrigley

apartment, Chicago

Top-Rated Pet-Friendly Vacation Rentals in Chicago

Explore the city with your dog from rentals located near the green stretches of Grant Park or Lincoln Park. These pet-friendly vacation rentals provide easy access to urban walking paths and local dog beaches along Lake Michigan.

Sunny & Spacious Private Apt In Artists Home - Chicago
10 71 reviews

Sunny & Spacious Private Apt In Artists Home

apartment, Chicago
New! Beautiful 7bd Home - Sleeps 15 + 2 Car Garage - Chicago
9.7 33 reviews

New! Beautiful 7bd Home - Sleeps 15 + 2 Car Garage

apartment, Chicago
Bright Family-friendly Lincoln Square 2-bed 1-bath - Chicago
9.9 431 reviews

Bright Family-friendly Lincoln Square 2-bed 1-bath

apartment, Chicago
Susie's Space. 2br Easy Parking & Pet Friendly - Chicago
9.8 388 reviews

Susie's Space. 2br Easy Parking & Pet Friendly

apartment, Chicago

Search Vacation Rentals with Swimming Pool in Chicago

Make a morning swim part of your routine with a luxury rental or Airbnb featuring an on-site pool. It’s the perfect way to recharge after a day of meetings or sightseeing at Navy Pier and the Art Institute.

Fully Furnished Gold Coast Luxury Condo With Sunset View Ideal For 30+ Day Stays - Chicago
No reviews

Fully Furnished Gold Coast Luxury Condo With Sunset View Ideal For 30+ Day Stays

apartment, Chicago
Luxury Designer Penthouse 3801 | Pool | Gold Coast - Chicago
9.6 75 reviews

Luxury Designer Penthouse 3801 | Pool | Gold Coast

apartment, Chicago
2bd River North Million Dollar Views! Parking Incl - Chicago
10 12 reviews

2bd River North Million Dollar Views! Parking Incl

apartment, Chicago
Downtown Penthouse 5bd Views | Parking, Gym+pool - Chicago
9.6 16 reviews

Downtown Penthouse 5bd Views | Parking, Gym+pool

apartment, Chicago

Explore Vacation Rentals with Jacuzzi in Chicago

Unwind in a private hot tub after a day of exploring the Loop or the boutiques in Wicker Park. These top-rated rentals offer a quiet sanctuary to relax while soaking in the energy of the city.

Top-floor Oasis: 2br In Heart Of Fulton Market - Chicago
10 1 review

Top-floor Oasis: 2br In Heart Of Fulton Market

apartment, Chicago
Spacious 1 Bd Sleeps 4 Quiet And Near Michigan Ave. Free Gift - Chicago
10 4 reviews

Spacious 1 Bd Sleeps 4 Quiet And Near Michigan Ave. Free Gift

apartment, Chicago
West Loop Studio~pool/gym! - Chicago
10 2 reviews

West Loop Studio~pool/gym!

apartment, Chicago
Scenic 3br Ph For Tourism + Prime Location - Chicago
10 2 reviews

Scenic 3br Ph For Tourism + Prime Location

apartment, Chicago